Tetrahydrofuran → 5-Morpholinopyridin-2-amine

Participants

Reaction Steps

A solution of 2-amino-5-bromopyridine (2.0 g, 0.011 mol) in t-butanol (5 ml) is degassed with nitrogen for 5 min. Morpholine (1.4 g, 0.016 mol), Davephos (0.4 g, 0.001 mol) and tris(dibenzylideneacetone)dipalladium(0) (0.25 g, 0.027 mmol) is added. A 1.6M solution of lithium bis(trimethylsilyl)amide in THF (5.51 g, 0.033 mol) is then added dropwise. The reaction mixture is irradiated in the microwave at 150° C. for 2 h. Water is added (30 ml), and the mixture is extracted with ethyl acetate (2×100 ml). The organic phases are washed with water (1×100 ml) and dried over sodium sulfate. The crude material is employed in the next step without purification. 5-Morpholin-4-ylpyridin-2-ylamine is employed in the synthesis of “A7”.

Provenance & Evidence